methyl 1-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate | 113967-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate
• 英文别名: 1-Methyl-1-methoxycarbonyl-1,2,3,4-tetrahydronaphthalin；methyl 3,4-dihydro-1-methylnaphthalenecarboxylate；methyl 1-methyl-3,4-dihydro-2H-naphthalene-1-carboxylate
• CAS: 113967-23-0
• 化学式: C₁₃H₁₆O₂
• mdl: MFCD25970531
• 分子量: 204.269
• InChiKey: WPQDZEYPGYMDAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以54%的产率得到methyl 1,2,3,4-tetrahydro-1-methyl-4-oxonaphthalene-1-carboxylate
  参考文献：
  名称：

  AN OPTIMIZED PREPARATION OF 2,3-DIHYDRO-1-METHYL-4-OXONAPHTHALENE-1-CARBOXYLIC ACID

  摘要：

  DOI：

  10.1080/00304940009355931
• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘甲酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 methyl 1-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  八千五百万岁久久琥珀中久久藤醇的两种对映异构体的合成及生物活性

  摘要：

  通过全合成确定降冰片烷萜类化合物，苦瓜糖醇（1）的完整结构。总合成的关键特征是（1）通过苯甲酰胺的邻位化来安装异戊基；（2）通过RCM反应构建四氢萘酮；（3）使用色谱分离法测定（±）-1的光学拆分度。相应的樟脑。从极性更大的樟脑酸酯获得的对-溴苯甲酸酯的X射线晶体学分析与天然衍生物相同，表明天然的苦瓜酚具有S-构型。天然对映体及其（R）-对映体对突变酵母和HL - 60细胞具有相同的抑制活性，而在C-8和（±）-1的9位上没有烷基的简单类似物则没有这种活性。

  DOI：

  10.1016/j.bmcl.2012.05.022

文献信息

• Antidepressant imidazolines and related compounds
  申请人：Sterling Drug Inc.

  公开号：US04540705A1

  公开（公告）日：1985-09-10

  2-(2-Naphthalenyl)alkyl-4,5-dihydro-1H-imidazoles and -tetrahydropyrimidines, the corresponding 3,4-dihydronaphthalenyl and 1,2,3,4-tetrahydronaphthalenyl compounds; and the corresponding indene and indane derivatives, useful as antidepressant or diuretic agents, are prepared by reacting the appropriate 2-(cyanoalkyl)naphthalene or -indane derivative (or the corresponding ester or imino-ether) with an alkylenediamine.

  2-(2-萘基)烷基-4,5-二氢-1H-咪唑和-四氢嘧啶，相应的3,4-二氢萘基和1,2,3,4-四氢萘基化合物；以及相应的茚和茚烷衍生物，可用作抗抑郁或利尿剂，通过将适当的2-(氰基烷基)萘烯或-茚烷衍生物（或相应的酯或亚胺醚）与烷二胺反应制备。
• Lewis Acid-Promoted Favorskii-Type Ring Contraction of Some Cyclic α-Bromo Ketones and Their Acetals
  作者：Swaraj B. Maiti、S. R. Ray Chaudhuri、Amareshwar Chatterjee

  DOI：10.1055/s-1987-28079

  日期：——

  The α-bromo cycloalkyl aryl ketones 2a-d on heating with zinc chloride in methanol furnished in moderate to good yields the ring-contracted products 3a-d having gem methyl carbomethoxy function. The acetals of the related α-bromo ketones 7a-c, lacking the methyl group on the halogen-bearing carbon atom, afforded in acceptable yields the ring-contracted esters 8a-c when heated in protic solvent. The limitation of the present ring-contraction procedure has been discussed.

  加热α-溴环烷基芳基酮2a-d与氯化锌在甲醇中反应，获得了中等到良好的产率的环收缩产物3a-d，具有gem-甲基碳甲氧基功能。相关的α-溴酮7a-c的醇醚，缺乏氯原子邻近的甲基，经过加热在质子溶剂中反应，获得了可接受产率的环收缩酯8a-c。对目前的环收缩反应程序的局限性进行了讨论。
• A Novel Synthetic Route to 2-Arylalkanoic Acids by a Ruthenium-Catalyzed Chemoselective Oxidation of Furan Rings
  作者：Keitaro Ishii、Masahiro Noji、Haruka Sunahara、Ken-ichi Tsuchiya、Tôru Mukai、Ayako Komasaka

  DOI：10.1055/s-0028-1083222

  日期：2008.12

  Friedel-Crafts alkylation of 2-methylfuran with 1-arylalkanols without employing anhydrous conditions. The chemoselective oxidation of the furan ring in 1-arylalkylfurans to carboxylic acid was then investigated. In a solvent system of hexane-EtOAc/H 2 O (1:3:4), the furan ring was selectively oxidized with 7 equivalents of NaIO 4 by using 0.5 mol% RuCl 3 as catalyst to give 2-arylalkanoic acids in good yields

  描述了一种从 1-芳基烷醇高效两步合成 2-芳基烷酸的方法。首先，通过金属三氟甲磺酸盐催化 2-甲基呋喃与 1-芳基烷醇在无水条件下的傅-克烷基化反应，以高收率合成 1-芳基烷基呋喃衍生物。然后研究了 1-芳烷基呋喃中的呋喃环化学选择性氧化为羧酸。在己烷-EtOAc/H 2 O (1:3:4) 溶剂体系中，以 0.5 mol% RuCl 3 为催化剂，用 7 当量 NaIO 4 选择性氧化呋喃环，以良好收率得到 2-芳基链烷酸. 钌氧化的选择性由己烷-EtOAc的溶剂比控制。
• Acetylenic cyanoenones as therapeutics for inflammation and carcinogenesis
  申请人：Honda Tadashi

  公开号：US10233146B2

  公开（公告）日：2019-03-19

  The present invention provides a compound having the structure: wherein X is C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, cyano, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkenylaryl, alkenylheteroaryl, alkynylaryl, alkynylheteroaryl, alkoxy, alkenyloxy, alkynyloxy, aryloxy, heteroaryloxy, acyl, alkylhydroxy, alkylamino, alkenylamino, alkynylamino, amido, carboxyl, or carboxyl ester, or forms an unsubstituted or substituted cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, indane or tetralin with Y, Y is H or forms an unsubstituted or substituted cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, indane or tetralin with X, or forms an unsubstituted or substituted monocycle with Z; and Z is H or forms an unsubstituted or substituted monocycle with Y; wherein when X and Y are both H, then X is C2 alkenyl or C2 alkynyl, and when Y is H forms a substituted cyclohexyl, cycloheptyl with X, the cyclohexyl is other than a trisubstituted cyclohexyl bearing CH3, i-Pr and (CH2)2CO2CH3 groups or CH3, i-Pr and (CH2)3NH2, or a salt or ester thereof.

  本发明提供了一种具有以下结构的化合物： 其中 X是C1-C12烷基、C2-C12烯基、C2-C12炔基、氰基、芳基、杂芳基、烷芳基、烷基异芳基、烯芳基、烯基异芳基、炔芳基、炔基异芳基、烷氧基、烯氧基、炔氧基、芳氧基、杂芳氧基、酰基、烷基羟基、烷基氨基、烯基氨基、炔基氨基、氨基、羧基或羧基酯，或与 Y 形成未取代或取代的环丁基、环戊基、环己基、环庚基、茚或四萘、 Y 是 H，或与 X 形成未取代或取代的环丁基、环戊基、环己基、环庚基、茚满或四萘，或与 Z 形成未取代或取代的单环；和 Z 是 H，或与 Y 形成未取代或取代的单环； 其中，当 X 和 Y 均为 H 时，则 X 为 C2 烯基或 C2 炔基，而当 Y 为 H 时，则与 X 形成取代的环己基、环庚基，该环己基是三取代的环己基以外的环己基。 当 Y 为 H 与 X 形成取代的环己基、环庚基时，环己基不是含有 CH3、i-Pr 和 (CH2)2CO2 基团或 、i-Pr 和 ( )3NH2 的三取代环己基、 或其盐或酯。
• New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase
  作者：Wei Li、Suqing Zheng、Maureen Higgins、Rocco P. Morra、Anne T. Mendis、Chih-Wei Chien、Iwao Ojima、Dale F. Mierke、Albena T. Dinkova-Kostova、Tadashi Honda

  DOI：10.1021/acs.jmedchem.5b00393

  日期：2015.6.11

  A monocyclic compound 3 (3-ethynyl-3-methyl-6-oxocyclohexa-1,4-dienecarbonitrile) is a highly reactive Michael acceptor leading to reversible adducts with nucleophiles, which displays equal or greater potency than the pentacyclic triterpenoid CDDO in inflammation and carcinogenesis related assays. Recently, reversible covalent drugs, which bind with protein targets but not permanently, have been gaining attention because of their unique features. To explore such reversible covalent drugs, we have synthesized monocyclic, bicyclic, and tricyclic compounds containing 3 as an electrophilic fragment and evaluated them as activators of the Keap1/Nrf2/ARE pathway and inhibitors of iNOS. Notably, these compounds maintain the unique features of the chemical reactivity and biological potency of 3. Among them, a monocyclic compound 5 is the most potent in these assays while a tricyclic compound 14 displays a more robust and specific activation profile compared to 5. In conclusion, we demonstrate that 3 is a useful electrophilic fragment for exploring reversible covalent drugs.